60-18-4
L-Tyrosine
CAS: 60-18-4;55520-40-6
Molecular Formula: C9H11NO3
60-18-4 - Names and Identifiers
| Name | L-Tyrosine |
| Synonyms | Tyr H-Tyr-OH NSC 9973 Tyrosine NSC 82624 L-Tyrosine p-Tyrosine tyrosine usp L-p-Tyrosine (S)-Tyrosine L-(-)-Tyrosine Tyrosine,L- (8CI) L-Tyrosine, Free Base L-Phenylalanine, 4-hydroxy- 3-(4-Hydroxyphenyl)-L-alanine L-tyrosine plant cell culture tested (-)-a-Amino-p-hydroxyhydrocinnamicacid L-tyrosine free base cell culture*tested (S)-a-Amino-4-hydroxybenzenepropanoicacid (S)-2-Amino-3-(4-hydroxyphenyl)propanoic acid (2S)-2-Amino-3-(4-hydroxyphenyl)propanoic acid Benzenepropanoic acid, a-amino-4-hydroxy-, (S)- Propanoic acid,2-amino-3-(4-hydroxyphenyl)-, (S)- |
| CAS | 60-18-4 55520-40-6 |
| EINECS | 200-460-4 |
| InChI | InChI=1/C9H11NO3/c10-8(9(12)13)5-6-1-3-7(11)4-2-6/h1-4,8,11H,5,10H2,(H,12,13)/t8-/m0/s1 |
| InChIKey | OUYCCCASQSFEME-QMMMGPOBSA-N |
60-18-4 - Physico-chemical Properties
| Molecular Formula | C9H11NO3 |
| Molar Mass | 181.19 |
| Density | 1.34 |
| Melting Point | 290℃ |
| Boling Point | 314.29°C (rough estimate) |
| Specific Rotation(α) | -11.65 ° (C=5,DIL HCL/H2O 50/50) |
| Flash Point | 176℃ |
| Water Solubility | 0.45 g/L (25℃) |
| Solubility | Insoluble in water (0.04%, 25°C), insoluble in absolute ethanol, ether and acetone, soluble in dilute acid or alkali. |
| Appearance | Morphological powder |
| Color | White to Pale-brown |
| Merck | 14,9839 |
| BRN | 392441 |
| pKa | 2.2(at 25℃) |
| PH | 6.5 (0.1g/l, H2O) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Incompatible with strong oxidizing agents, strong reducing agents. |
| Sensitive | Sensitive to light |
| Refractive Index | -12 ° (C=5, 1mol/L H |
| MDL | MFCD00002606 |
| Physical and Chemical Properties | The product is mercerized fine needle-like crystal or crystalline powder. Melting point ≥ 300 °c. 342~344 degrees C decomposition. In the coexistence with hydrocarbons are more susceptible to decomposition. Density 1.456g/cm3. pK '12.20;pK' 29.11;pK '310.07. Optical rotation -10.6 °(c = 4 in 1mol/L HCl);-13.2 °(c = 4,3mol/L NaOH). -12.3 ° ± 0.5 °,-11.0 ° ± 0.5 °(c = 4, 1 mol/L HCl) solubility in water (g/100ml):0.02(0 °c);0.045(25 degrees C);0.105(50 degrees C);0.244(75 degrees C);0.565(100 degrees C). Soluble in aqueous alkali solution. Insoluble in neutral organic solvents, such as ethanol, ether, acetone, etc. |
| Use | For tissue culture (L-tyrosine · 2Na · H2O), biochemical reagents, treatment of hyperthyroidism. Can also be used as a modulation of the elderly, children's food and plant foliar nutrition, etc |
60-18-4 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | YP2275600 |
| TSCA | Yes |
| HS Code | 29225000 |
| Toxicity | LD50 orally in Rabbit: > 5110 mg/kg |
60-18-4 - Upstream Downstream Industry
60-18-4 - Application
Introduction
Tyrosine (Tyr or Y), or 4-hydroxyphenylalanine, is one of the 22 amino acids that cells use to synthesize proteins, its codons are UAC and UAU, which are non-essential amino acids containing polar side groups that can be synthesized by the human body. The word "tyrosine" is derived from the Greek tyros, meaning cheese. At the beginning of the 19th century, it was first discovered in the presence of casein in the presence of Es by the German chemist Ustus von lebich, and when used as a functional or side group, it was called tyrosyl.
function
In addition to being a protein amino acid, in the process of signal transmission in proteins, tyrosine has a special role by virtue of its phenolic functional group, which functions as a protein kinase (the so-called tyrosine kinase receptor) the signal transfers to the receptor of the phosphate group, while the phosphorylation of the hydroxyl group changes the activity of the target protein.
tyrosine also plays an important role in photosynthesis, in the chloroplast (photosystem II), in the reduction reaction of oxidized chlorophyll as an electron provider, this was subjected to deprotonation of the phenolic OH-groups and finally reduced by the four core manganese clusters in photosystem II.
dietary sources
Tyrosine is synthesized in the body from phenylalanine and can be found in many high protein foods such as chicken, turkey, fish, milk, yogurt, cheese, cheese, peanuts, almonds, pumpkin seeds, sesame seeds, soybeans, lima beans, avocados and bananas are found.Last Update：2025-08-19 16:24:40
60-18-4 - Biosynthesis
In microorganisms or plants, tyrosine is produced through prephenic acid, an intermediate product of the shikimic acid reaction pathway, the oxidative decarboxylation of prebenzoic acid with the retained hydroxyl groups gives p-hydroxyphenylpyruvate, and tyrosine and α-ketoglutarate are transaminated using glutamic acid as a nitrogen source to produce P-hydroxyphenylpyruvate.
mammals use the essential amino acid phenylalanine (PHE) from food to synthesize tyrosine. The conversion of phenylalanine to tyrosine is catalyzed by alanine hydroxylase, a monooxidase, this enzyme-catalyzed reaction causes an addition reaction of the hydroxyl group and the aromatic ring end of the 6-carbocyclic ring of phenylalanine, making it tyrosine.
Last Update：2023-08-17 00:16:37
60-18-4 - Nature
Open Data Verified Data
- This product is white needle-like crystal or crystalline powder with bitter taste. Melting point 344 °c (decomposition). Slightly soluble in water (0.04%,25 ° C), insoluble in ethanol, ether and acetone, soluble in alkali solution. The pure product is stable, and the coexistence of hydrocarbons is easy to decompose.
- L-tyrosine is an aromatic amino acid and is a non-essential amino acid. In vivo, by L-phenylalanine hydroxylation or by the branch acid, hydroxyphenylpyruvic acid synthesis, decomposition is through the hydroxyphenylpyruvic acid into fumaric acid and acetoacetic acid metabolism. Can promote catecholamine, thyroid hormone, melanin biosynthesis, and plant nerve, endocrine function is closely related.
Last Update：2025-06-10 22:55:16
60-18-4 - Preparation Method
Open Data Verified Data
- extraction method.
- direct fermentation method.
- enzymatic method.
Last Update：2022-01-01 11:10:26
60-18-4 - Introduction
L-tyrosine is a non-essential amino acid with polar side chains. Cells can use it to synthesize proteins that play a role in signal transduction. L-tyrosine is a proteogenic amino acid that acts as a receiver of the phosphogroup transferred by the kinase.
Last Update：2022-10-16 17:26:55
60-18-4 - Metabolic reaction
phosphorylation and sulfation
some tyrosine can be labeled with the phosphate group of protein kinase, tyrosine in phosphorylated form is called phosphotyrosine, tyrosine phosphorylation is considered to be one of the key steps in signal transduction and regulation of enzyme activity, phosphotyrosine can be detected by specific antibodies, and tyrosine can also be modified by added sulfate groups. This reaction process is called tyrosine sulfation. Tyrosine sulfation is catalyzed by the sulfotransferase (TPST) enzyme in the tyrosyl protein, which, like the phosphotyrosine antibody mentioned above, has the specificity to detect sulfotyrosine.
precursors of neurotransmitters and hormones
In dopamine cells in the brain, tyrosine is converted to L-dopamine by the enzyme tyrosine hydroxylase (TH), a rate-limiting enzyme, it is used in the synthesis of the neurotransmitter dopamine, which is converted into the catecholamines norepinephrine (noradrenaline) and epinephrine (adrenaline).
The thyroid hormone triiodothyronine (T3) and thyroxine (T4) in the thyroid colloid are also derived from tyrosine.
Chemically, epinephrine is one of a group of monoamines called catecholamines. It is produced from the amino acids phenylalanine and tyrosine in some neurons of the central nervous system, and in the chromaffin cells of the adrenal medulla.
precursors of alkaloids
latex in the hypnotic substance of Papaveraceae, also known as Papaver, has been shown to convert tyrosine into the alkaloid morphine, in its biosynthetic reaction pathway, tyrosine traces the in vivo synthesis pathway using carbon -14 radiolabeled tyrosine.
tyrosine biosynthesis in cactus produced by trimethoxyphenethylamine.
precursors of natural phenols
Tyrosine ammonia lyase (TAL) is an enzyme in the natural phenol biosynthesis reaction pathway that converts L-tyrosine to coumaric acid.
precursor of pigment
tyrosine is also a precursor of melanin in the pigment.
degradation
tyrosine is broken down into acetoacetic acid and fumaric acid. Two dioxygenases are necessary in the decomposition process, and the final product will enter the citric acid cycle.
The decomposition of L-tyrosine (p-hydroxyphenylalanine) is a dependent transfer reaction of tyrosine transaminase into α-ketoglutarate of p-hydroxyphenylpyruvate, the binding position of which is Para, abbreviated as p, it indicates that the hydroxyl group and the side chain on the benzene ring are in opposite orientation (see figure below).
The next oxidation step is catalyzed by the cleavage of p-hydroxyphenylpyruvate-dioxygenase and carbon dioxide urinary black acid (2, 5-dihydroxyphenyl-1-ethyl acetate), in order to unravel the aromatic ring of urinary black acid, further binding by oxygen molecules to obtain urinary black acid oxygenase is necessary.
The rotation of the carboxyl groups caused by the oxidized hydroxyl groups by fumaryl acetic acid produces the maleylacetoacetate-cis-trans isomerase. The glutathione-containing cis-trans isomerase acts as a coenzyme, and the fumaryl Acetoacetate is finally cleaved by the fumaryl acetoacetate hydrolase by adding a water molecule.
fumarate (also a metabolite of the citric acid cycle) and acetoacetate (3-butanoic acid) are in the Free State, it can be converted to acetyl-CoA upon activation by succinyl-CoA, which in turn can be oxidized cyclically by citric acid or used for fatty acid synthesis.
Phloretic acid is also tyrosine of the urinary metabolite in rats.
Last Update：2023-08-17 00:16:41
60-18-4 - Application
Open Data Verified Data
amino acid drugs. Amino acid infusion and amino acid compound preparation of raw materials, as nutritional supplements. Treatment of poliomyelitis and sex nuclear encephalitis, hyperthyroidism and other diseases. It is also used as a raw material for the manufacture of diiodotyrosine, dibromotyrosine and L-dopa.
Last Update：2025-08-19 16:24:40
60-18-4 - Production process
I. Alkali-soluble segment
Raw material: Tertiary mother liquor (product of tertiary neutralization in production of L-cystine)
Excipients: liquid alkali, pure water, activated carbon
The third mother liquor is passed into the alkali dissolution tank, and liquid alkali, pure water, activated carbon, temperature 90, alkali dissolution time 6h, and filtered.
End product: 1, filter residue (recycling) 2, filtrate (to one neutralization stage)
second, first neutralization
Excipient: Hydrochloric acid
The filtrate was fed into a primary neutralization tank, and hydrochloric acid was passed through, the temperature was 80, the neutralization time was 6h, the end point PH = 8.5, and filtered.
End product: 1, filtrate (recycling) 2, filter residue (decolorizing section)
Three, decolorization section
Excipients: hydrochloric acid, steam, pure water, activated carbon
The filter residue enters the decoloring tank, and hydrochloric acid, steam, pure water, activated carbon, temperature 80, decolorization Time 2h, end ph = 0.5, is filtered.
End product: 1, filter residue (recycling) 2, filtrate (to secondary neutralization stage)
Four, secondary neutralization segment
Excipient: ammonia
Filtrate into the secondary neutralization tank, into the ammonia, temperature 80, neutralization Time 4H, terminal ph = 4.0, crystallization, filtration
End-point product: 1, filtrate (recycling) 2, filter residue (I. E. Crude L-tyrosine, derefining section)
V, refined segment
Excipients: distilled water, steam
Rinse the product of the previous step with distilled water and spin dry it by centrifugation, send it to the dryer, dry it with steam, package it, store it in the warehouse, dry it at a temperature of 100, atmospheric pressure of -0.09Mpa, and dry it for 5H.
end product: L-tyrosine finished product
Last Update：2023-08-17 00:16:46
60-18-4 - Safety
Open Data Verified Data
there is no side effect when the patient takes 20g per day. Sealed and preserved in the dark.
Last Update：2022-01-01 11:10:27
60-18-4 - Effect on the skin
The skin is not white, mainly depends on the ability of melanocytes to synthesize melanin. In the human epidermal cells, the distribution of melanocytes, it contains tyrosinase can be oxidized into tyrosine polysaccharide, intermediate after a series of metabolic processes, and finally can produce melanin. The more melanin is produced, the darker the skin; Conversely, the whiter the skin.
studies have shown that tyrosinase activity is closely related to copper, iron, zinc and other elements in the body. Often eat substances rich in tyrosine and rare elements of zinc, copper, iron, such as animal viscera, kidney, crustacean clams, crab, river snails, oysters, aquatic products black fish, beans, lentils, green beans, red beans, hard shell fruits such as peanuts, walnuts, black sesame seeds and currants, the color of the skin is black. Therefore, people living by the sea, fishing fishers, due to eat more aquatic products, so the skin is black.
Last Update：2023-08-17 00:16:10
60-18-4 - Use Supplement
- amino acid drugs. Amino acid infusion and amino acid compound preparation of raw materials, as nutritional supplements. For the treatment of polio and tuberculous encephalitis/hyperthyroidism and other diseases.
- a special flavor substance can be generated after the aminocarbonyl reaction occurs with the co-heat of the saccharide.
- medically used for the treatment of hyperthyroidism.
- used in biochemical research, medicine as amino acid nutrition drugs, treatment of polio, encephalitis, hyperthyroidism and other diseases.
- nutritional supplement. Medicine for the treatment of myelitis and tuberculosis encephalitis, hyperthyroidism and other diseases, also for the manufacture of L-dopa diiodotyrosine. After the amino carbonyl reaction occurs with the sugar, a special flavor substance can be generated.
- Biochemical reagent, drug substance. Belongs to the human body non-essential amino acids.
- can be used for tissue culture (L-tyrosine · 2Na · H2O), biochemical reagents, and treatment of hyperthyroidism. Can also be used as a modulation of the elderly, children's food and plant foliar nutrients, etc.
Last Update：2024-04-10 22:29:15
60-18-4 - Production method supplement
| The precipitate obtained by neutralization of a protein acid hydrolysate such as casein and silk was separated, dissolved in dilute aqueous ammonia, neutralized to pH = 5 with acetic acid, and recrystallized. Extract the second crude crystal pure liquid of cystine from pig hair hydrolysate, store it below 20 ℃ for 2 days, precipitate tyrosine, filter, and obtain crude tyrosine, L-tyrosine can also be obtained by purification. The yield to pig hair was 1%. |
| with casein as raw material, hydrochloric acid reflux for several hours, after filtration, concentration, alkali neutralization, activated carbon treatment, crystallization to get the product. |
| a precipitate obtained by neutralization of an acid hydrolysate of a protein such as casein or spun silk is separated, dissolved in dilute aqueous ammonia, and neutralized with acetic acid to a pH of 5, and then recrystallized. |
| L-tyrosine is mainly prepared by protein hydrolysis extraction method. Can be used pig blood powder, hoof, silk and other raw materials, acid hydrolysis, and then separation and purification. Pig blood powder [HCl (hydrolysis)]& rarr;[110 ℃, 24h] hydrolysate [acid removal] & rarr;[evaporation concentration] acid removal solution [activated carbon] & rarr; decolorizing liquid [decolorization, cooling crystallization] & rarr;L-tyrosine crude [activated carbon (refined)]& rarr;[90 ℃, 30min] filtrate [crystallization] & rarr;L-tyrosine. Hydrolysis and acid removal the pig blood powder, water and industrial hydrochloric acid are put into the hydrolysis cylinder respectively according to the weight ratio of 1:1.3:1, heated to 112-114 ℃, stirred and refluxed for 24h and then stopped, the filtrate is obtained by cooling and filtering to remove the hydrolysate. The hydrolysate was evaporated and concentrated to a syrup form, and then water was added to dissolve and evaporated to concentrate. This was repeated three times to remove acid. Decolorizing and crystallizing concentrated solution is diluted with distilled water until it is completely dissolved, and then Shen ammonia water is added to adjust the pH value of the solution to 3.5, 1% activated carbon is added, the solution is stirred and boiled for 10min, and the mixture is kept for 30min In a water bath at 90 ℃, after hot filtration, the activated carbon layer was washed three times with distilled water, and the filtrate and washing liquid were combined. According to this method, the decolorization with activated carbon was continued until the solution was pale yellow in color. The filtrate was left standing at 10 ° C. Or less for 24h to precipitate crystals, and the crude L-tyrosine was obtained by filtration. Recrystallization purification the crude tyrosine was added into distilled water at 1:20 to dissolve it completely, then 1% activated carbon was added, and the mixture was stirred at 90 ° C. For 30min, and filtered while hot. The filtrate was cooled and refined to precipitate crystals. The crystals were filtered, washed twice with absolute ethanol, and dried at 60 ° C. To obtain a finished product of L-tyrosine. |
Last Update：2024-04-09 21:01:54
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